Any referrals or recommendations for good and qualified brokers, sellers, property management companies, loan brokers, insurance brokers, mortgage brokers, contractors, etc.

I recommend Steadily - PM me if you want a link. 

I made a fair size claim last year and it paid off pretty painlessly except for the 90 day lag. highly recommend them.If I had used a regular home owners policy with and STR addendum I'm pretty sure it would not have covered my particular issue.

This is what I recommend to new investors who contact me asking if these numbers look good. 

Using 50% rule (expenses excluding P&i is 50% of rent) here are the numbers;1800 (rent) - $900 (expenses) - 1468 (heloc) = negative $568/monthAt your rent point with that size unit, your expenses will ve less than depicted by the 50% rule, so let’s use a likely more accurate 40%1800 - 720 (expenses) - 1468 = negative $388/monthNow let’s imagine you self manage and you time is not worth anything (I strongly recommend believing your time is worth less or worth less than a quality PM would charge) with 8% further reduction so expenses are down to 32%1800 - 576 (expenses) - 1468 = negative $244/month. 

Can anyone recommend any sites, courses, videos, or books to purchase so I can prepare for the test?

I would recommend you begin researching Chicago based meetups as there are a bunch of really good ones.

Hey Sam,Congratulations, hopefully you can work something out.My recommendation would be working with a lender that is comfortable with seller financing and keep your cash to close at a minimum.

At appraisal it was worth $500K and it is in a neighborhood where homes that are on a third the size of the lot are going for $800K.What's the best way to get a loan, about $150K, to rehab his house and get it ready to sell. as mentioned, I recommend getting a loan to rehab the property.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?